This invention relates to novel intermediates and method for the chemical synthesis of N-substituted 1,5-dideoxy-1,5-imino-L-fucitol derivatives.
The polyhydroxylated piperidine, 1,5-dideoxy-1,5-imino-L-fucitol, is a potent competitive inhibitor of .alpha.-L-fucosidase, although it has no inhibitory action on a range of other glycosidases. The synthesis of 1,5-dideoxy-1,5-imino-L-fucitol from commercially available methyl .alpha.-D-glucopyranoside is described by Fleet et al., J. Chem. Soc., Chemical Communications 13, 841-842 (1985). It is also useful in the production of inhibitors of the human immuno-deficiency virus (HIV) as described in co-pending application Ser. No. 136,219, filed Dec.21, 1987 now abandoned. One such HIV inhibitor is the following N-substituted derivative of 1,5-dideoxy-1,5-imino-L-fucitol: ##STR1##
This derivative was prepared by reaction of 1,5-dideoxy-1,5-imino-L-fucitol in methanol solvent medium with 6-oxyhexanoate.